[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C@H:10]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:11][CH2:12][S:13][CH3:14])=[CH:4][CH:3]=1.[CH3:27][I:28]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:26])[C@H:10]([NH:15][C:16]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[CH2:11][CH2:12][SH:13]([CH3:27])[CH3:14])=[CH:6][CH:7]=1.[I-:28]To neat (2R)-N-(4-chlorophenyl)-4-methylthio-2-[(phenylmethoxy)carbonylamino]butanamide (2.0 g, 5.09 mmol) was added methyl iodide (10 ml, 161 mmol). The solution was allowed to stir for 48 hours. Methyl iodide was then removed under vacuum to yield (2R)-N-(4-chlorophenyl)-5-methyl-2-[(phenylmethoxy)carbonylamino]-5-thiahexanamide, iodide.
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